Career Advice From J.Crew President and Creative Director Jenna Lyons

She started at J.Crew as an "assistant to an assistant" 25 years ago. Now the brand's iconic Jenna Lyons shares the lessons she's learned with Glamour's Cindi Leive.

Just a few things you may already know about Jenna Lyons, famously nicknamed The Woman Who Dresses America by The New York Times: She made glasses, bright lips, and that sequins-with-denim thing cool. She's a First Lady favorite. And she proved once and for all that great fashion can come at all prices. But Jenna Lyons (born Judith, by the way) is also a woman who knows a lot about pursuing your dreams: She started at J.Crew in a job so lowly her desk was in the hallway; today, as group president and executive creative director there, she calls the shots. With her company suddenly in the hot seat (net income fell 8 percent in 2014), Lyons, 47, sat down with me in her chic office for a candid discussion of how she tunes out the noise — and other career strategies we all should know.

Cindi Leive: So many male designers initially approach fashion as "art," but your first designs were for yourself — you made clothes that made you feel good. Tell me about those early days.Jenna Lyons: I lived in a small town. I was certainly not very cool, the outcast. Sewing classes were the thing that clicked for me — making clothes that worked on my body type, because I was so tall. There was nothing about my life that made me think I could be in the fashion world. It was more like, I can't find anything to wear!

CL: And people complimented you on what you wore, right?JL: A girl in social studies passed me a note saying, "I like your skirt." I was like, Is this for me? It was major.

CL: You're marking your 25th year at J.Crew. Going back 25 years, what did you learn from those assistant days?JL: The thing I think is most important for young people to know is that today there's this idea of having everything quickly, that you're going to walk in the door, be a designer, and not have to do any of the grunt work. It's just not realistic. The things you don't learn in school are the skills you probably need more: what it's like to work with other people, how you build a team and collaborate.

CL: How did you learn those things on the job?JL: You learn to be a good boss by being a subordinate ... You realize, "Wow, it feels really good when somebody compliments me." Or when someone takes out their frustration on you, it's like, "OK, I'm not going to do that."

CL: I've heard that when Mickey [Drexler, the chairman and CEO of J.Crew Group] came to J.Crew in 2003, basically everyone had to reinterview for his or her job. How did you nail the interview?JL: I had nothing to lose other than to say exactly what I felt, because I could trust my instincts with him, which was great. We had a unified vision ... Prior to Mickey's arrival, it was hard to trust my gut. My confidence waned. I think I wasn't as good at my job.

CL: So you do your best work when you're surrounded by the best people for you.JL: I think so. And the best people for you have shared ideals — as soon as that is not the case, it's really hard to make decisions. One of the things I love about Mickey is, you know, we've gone through many business cycles that haven't always been great, but he always remains positive. He's like, "We know what we're doing. We didn't get stupid overnight. Let's just keep moving forward."

CL: During the first 10 years with you in a leadership position, revenue tripled ... Looking back, what accomplishments make you proudest?JL: Sometimes it's the small stuff. I remember this woman wrote me a letter and said she had to give a speech and was incredibly nervous. She had gone into J.Crew and got something to wear, and people said, "You look great!" She said, "I'm a scientist, I've never had anybody compliment me on my clothing before."... I do think sometimes people assume that what you wear isn't important, but I know it can make someone who needs a little boost feel beautiful.

CL: A lot has been written about J.Crew's revenue being down. How do you keep your team focused on the work and not the coverage?JL: Yeah, listen.... I remember Mickey saying very early on, "If you believe the good, you have to believe the bad. So don't read any of it." While it hurts and it's not fun, you have to remember that everyone's a critic these days. At the end of the day, I'm doing this because I enjoy it.... Whether the articles are good or bad, I get paid to play with sequins and color and cashmere, and that's awesome.

CL: I do have to ask about the much-maligned Tilly sweater [singled out as a problem by Drexler and others]...JL: I know, poor Tilly! It kept getting mentioned over and over again. We had had misses in our sweater business, so it sort of became the beacon for the miss. It took on a life of its own.

CL: So we're not blaming the Tilly?JL: The Tilly has to take some responsibility, as we all do in this building.

CL: So many women want to start their own businesses now — they're really passionate. How do you handle a setback when what you're doing is so personally on you?JL: I liken a perfect business run to winning the lottery: People's expectations are so high. But if you look at business...the mistakes often end up being the best things that could have happened. The only sad part about down business is if you don't learn from it, you know? Get in there and be humble. If you've had a great run, now's the time to sit back and put down your feathers. [Laughs.] I grew up in California; there were a lot of peacocks.

CL: Any advice for a woman who wants a job working for you?JL: Send me some of your work or a nice letter, and tell me why you're interested in working here. Don't send me an email ... You have to be old-school. Be professional.

CL: How about advice for moving up?JL: The person who makes herself indispensable, that's the person you want to promote. But when someone comes in and starts asking — it's such a disease. Demanding, "I've done all this and I want X," doesn't work for me so much. [Instead] ask questions: "I'm ready to take it to the next step. What is it that I can do better?" That, to me, is an engaged, collaborative way to get somebody to the next level. You're not going to get there just because you think you're ready or because someone else got promoted. We don't sit here and create a scale where we carefully ratchet everyone up evenly. Because if that were the case, we'd all be drones. No one is a drone ... You are you.

CL: Where do you see yourself in another 25 years?JL: Oh my God...I've got my wheelchair designed! It's going to be powder-coated in neon orange.